Places to Go in the Mid-Atlantic: Chestertown

Voted “The Best Small Town in Maryland to Chill Out” by WorldAtlas, Chestertown is a tiny burg with a population of less 6,000 but plenty of things to see and do. Starting out as one of Maryland’s Six Royal Ports of Entry in 1706, the riverside town is full of historic landmarks and boasts an active, thriving arts community.

From kayaking on the Chester River to enjoying a stage show at the Garfield Center for the Arts, there’s always something new to do in Chestertown.

Local Attractions

Chestertown might be most well-known for its annual festivals, which are steeped in its local history and culture. The most famous is likely the Chestertown Tea Party Festival, which is usually held on Memorial Day Weekend. While it includes plenty of fun festival staples like a 5k, a parade and live music, the piece de resistance is the historical reenactment of the Chestertown Tea Party, a 1774 protest held in response to the Boston Tea Party the year before.

During the summer, Chestertown hosts the Kent County 4H Fair, and in the fall, the Sultana Downrigging Weekend Tall Ship and Wooden Boat Festival attracts hundreds of naval enthusiasts and historic boat-owners, who take to the sea in celebration of the area’s boating history. For the rest of the year, the Sultana Schooner regularly sails the Chesapeake Bay as part of the Sultana Education Foundation, teaching students about environmental science.

Of course, there’s always plenty to do throughout the year, whether there’s a festival going on or not. Chestertown’s Arts and Education district features several unique galleries for the artistically-inclined to explore, and Wilmer Park is a common spot for community events and outdoor recreation like boating. There’s also the Washington College campus, which houses several attractions of its own.

Shopping

Chestertown’s Main Street is home to a diverse and eclectic array of locally-owned stores. For bookworms, there’s the independent bookstore The Bookplate—and for cat-lovers, you can stop into the store to meet its resident shop cat and mascot, Keke. For over 20 years, The Bookplate has prided itself on selling banned books and often hosts speaking engagements and signings with local authors.

If you’re looking for a date night outfit or just want to go thrifting to see what you can find, there are several clothing stores. These include menswear at Jerry Moe’s, clothes for your littlest family members at Tiny Tots Boutique, secondhand treasures at Empty Hangers Consignment Boutique and cozy sweaters at Walnut & Wool.

Every Saturday, the Chestertown Farmers and Artisans Market is a great way to discover local businesses and get ideas for recipes.

And for more daring shoppers, Dixon’s Crumpton Auction has been a staple in town for generations. You never know what kind of vintage furniture, jewelry or collector’s items might be up for sale at their biweekly auctions—they even sold a collection of original “Star Trek” scripts earlier this year.

Food

A lot of restaurants in Chestertown close fairly early in the evening, making it the perfect place to go out to lunch or have an early dinner. Chestertown is renowned for its crab soup, and one of the most beloved places serving it is The Kitchen at the Imperial. If you’re in town on Sunday mornings, they also offer a sizable brunch menu—and you can add a crab cake to any of their salads.

If you’re in the mood for a different kind of seafood, The Retriever Bar offers a raw menu of oysters sourced from all over Maryland and Virginia. And if you’re not into the idea of eating your oysters raw, you can also order them pan-roasted with sweet scallops or steamed in miso and garlic with mushrooms.

Want something heavier and more meaty? While Phat Daddy’s BBQ originated in Glen Burnie, its Phat Daddy’s BBQ Shack location in Chesterville smokes and barbecues its meats on-site, making for sandwiches piled high with specialties like pit beef and turkey.

No matter what you decide to eat, you can always top it off with a visit to Sugar Doodles Sweet Shop. Here, you can find crazy milkshakes piled high with whipped cream, cookies and Pop Tarts … and slightly healthier treats like acai bowls.